The development of rapid, cost‐effective, accurate methods for environmental site characterization and monitoring has been a very active area of research during the past two decades. One approach that has recently received widespread attention involves the use of cone penetrometer technologies for in situ detection and mapping of environmental contaminants in subsurface soils and groundwater. The most recent technological developments include the incorporation of on‐line analytical and in situ chemical detection techniques into the cone penetrometer. This article describes a variety of sampling and chemical sensing technologies that have been or are currently being adapted to cone penetrometer systems for the detection of subsurface contaminants, including petroleum, oils, and lubricants (POLs), volatile organic compounds (VOCs), toxic metals, explosives/energetics, and radioactive wastes. For example, cone penetrometer devices that incorporate in situ isolation techniques to purge VOCs from groundwater eliminate the analysis of the sample media in the laboratory. A high level of agreement was found between an in situ purging technique and the conventional method of bailing a sample from a groundwater sampler, transferring the sample to a container, and analyzing the sample in the laboratory. Completion of a site characterization with this probe was estimated to require approximately 15% of the time needed for conventional methods, significantly reducing costs. The laser‐induced fluorescence (LIF) sensor, which measures POLs, represents the first and most mature cone penetrometer chemical detection technology. Technology evaluations estimated that costs of site characterizations using the LIF probe are approximately 50% lower than costs of site characterizations using conventional methods for collecting soil cores, subsampling the cores, and analyzing the subsamples in the laboratory.